


OOPS! My Sugar Daddy is Also My Dad's Mortal Enemy!

by orphan_account



Category: Hamilton - Miranda
Genre: (past) - Freeform, Alternate Universe - Modern Setting, Alternate Universe - Sugar Daddy, Anxiety, BDSM, Daddy Kink, Depression, Discipline, Dom/sub, Genderqueer Character, Heart Attacks, Homophobia, Implied/Referenced Child Abuse, Implied/Referenced Domestic Violence, Jane Jefferson's A+++ Parenting, Light BDSM, M/M, Mental Health Issues, Non-Consensual Electroconvulsive Therapy, Other, Peter Jefferson's A+++ Parenting, Pip is Genderflux, Spanking, This isn't as heavy as it sounds, Threesome - M/M/M, Transphobia, but this went from sex to something more right quick, heed these tags yo, it's pretty great, the noncon isn't between pip and tom by the way
Language: English
Status: In-Progress
Published: 2017-07-30
Updated: 2017-07-31
Packaged: 2018-12-08 06:28:14
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, Rape/Non-Con
Chapters: 3
Words: 2,095
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11640849
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: This was originally a HIGHLY sexual RP, so if things are weird or things aren't developed on... You know why. This'll be updated as it goes on.----Basically what it says on the tin. Mostly porn.





	1. Chapter 1

**Author's Note:**

> Short first chapter, because... *Insert good reason*
> 
> Enjoy. Or don't. I can't make you.

Thomas Jefferson was _not_ at fault for this. For any of this. Okay, yes. He filled out his account details, he sent the first message, and he also said 'yes' to the first date. But it wasn't like he was expecting all of this to happen. And boy - was it a lot.

 

After significant goading from James ("No, Thomas, your only love can't be Kraft Mac 'n Cheese. You need to meet somebody.") he decided to sign up for a sugar daddy website. Sure, it was a little bit... unconventional, but he was getting on a bit in life and had money. He had always liked younger men, anyway. They usually had more of a desire to be taken care of, which was great for a multi-billionaire who loved spoiling the four people in his life he actually loved.

 

' _Name_ : _Thomas Jefferson_

 

_Age: 40_

 

 _Occupation_ :'

 

He can't help but hesitate. He has a dayjob, but he doesn't actually  _need_ to work. He works because he would be bored if he didn't and literally no other reason. He's got people that take care of his inherited assets. All that they need from him is an occasional signature. He decides to keep it cryptic - nothing too specific.

 

' _Businessman_

 

_Sexuality: Gay_

 

_Bio: Looking for a generous, mutually exclusive arrangement with a pretty young man who can keep up, doesn't mind RomComs, and likes macaroni and cheese.'_

 

He hits post, letting go of a breath he didn't even realize he had been holding. He doesn't know what he was expecting to happen. Maybe he would get dragged back to hell where he came from? No, that's ridiculous. Not as ridiculous as the rest of this entire thing, though. Papa and Mama would shit themselves. May as well get some use out of the damn thing. He microwaves some Velveeta, settles down on his couch, and flips through pictures of half-naked young men. 

 

Holy fuck. Holy fucking goddamn shit in hell. This kid  _hot_. Hot as all hell. He's wearing nothing but boxer briefs that reveal freckles basically everywhere, very limited body hair, and a body that was sculpted by God himself. He's so cute, like a puppy, but he's like hot at the same time. You can describe it however you want, but it's doing things to Thomas that are anything but holy. Okay. Send a message. It's not that hard. Just write something.

 

_Hi. Your profile is... intriguing, and I'd love to get to know you better._

 

 _'Send it, Jefferson. You've sent personal emails to Senators'_ He does. He can't overthink this one. Sex isn't something that you have to obsessively overthink. This probably wasn't what James had in mind, but it beats not having any social contact outside of arguing with Hamilton and awkward meetings. 


	2. Chapter 2

**Summary for the Chapter:**

> Philip's POV of the last one and some shifting POV + also some actual plot progression... WHAT?

**Notes for the Chapter:**

> This mostly just a pre-porn chapter.

Philip sighed softly, blinking at his laptop as he put his email address into the form he was filling out. Oh god, he couldn't believe he was doing  _this_ , which of course, was signing up for a damn sugar daddy website. What the hell was he thinking? His parents had money, he could simply ask for some if he wanted, but... he always felt bad asking for money that he hadn't earned. Plus, he had a little free time outside of classes because he had never been one for the party scene. Having sex in said time didn't sound like the worst thing he had ever done, especially after George had dumped him. 

 

So, yeah. He was doing this. He was signing up for a damn sugar daddy site, filling in most of the required fields like second nature. 

 

_'Name: Philip_

_Age: 19_

 

_Sexuality: Gay_

 

_Occupation: Student_

 

_Bio: Hey, I'm Pip, and'_

 

He didn't type out the rest of it, biting his lip nervously. He wanted to catch someone's attention... He needed this money.

 

_'Hey, I'm Pip. As you can see, I'm in college right now and I'm looking for someone that can help me with paying for it in exchange for... Negotiated benefits. I'm open to trying pretty much anything but do know, I can be a bit disobedient._

 

_XXX, Pip'_

 

He pressed submit, smiling as he looked over his profile. If he was lucky, the photo of him in his underwear would be enough to draw in a couple of guys. he was cute! Of course it would!

 

He was writing a paper when he got a notification for the message. Hell... his profile hadn't even been up for four hours! He opened his inbox, opening yet another tab in Chrome. He really needs to sort through all of those. 

 

He hums, skimming over the message and smiling a little. He waited to reply, clicking on the name of this 'Thomas'. He almost chokes on his coffee when he sees the few pictures of him because  _fucking hell_ , he was gorgeous. Honestly, Pip had always been into older guys, but damn... He was originally doing it just for the extra cash, sex was just a questionable plus, but if he got paid to have sex with this guy? Fuck yeah.

 

He went back to the message, quickly spitting out a reply so that he wouldn't lose Thomas's interest. 

 

_Really now? I'd really like to get to know you, too. Do you want to meet for coffee?_

 

A public space would be best, right? Then he wouldn't get raped or kidnapped or whatever weird shit older guys were into. 

 

-

 

Thomas can't help but hum to himself a little. He's going to get fucking  _laid._ The last time he had sex was during that two month fling with Laf. The sex was great, but the dating and other non-sex aspects had been awful, like he had been going out with himself. 

 

_Sounds great. I know a great place right by my office. I can send a car, or pick you up, or pick you up, or pay your taxi fare, or get you an uber...?_ He doesn't know what to offer, mostly because he doesn't want to turn him off. Then it suddenly occurs to him that Philip is only interested in his money. He's a college student, at  _Columbia_ no less. There's no way he isn't flat on his ass broke. Worst case scenario is that he gets to have coffee with a really hot, much younger guy.

  
Best case is, of course, is they form a solid relationship on the basis of fucking for money and grow old together and get eaten by their cats.

  
Wait, that's definitely not the best case. What the fuck? This kid is turning his fucking brain into mush. Thomas runs his hands through his hair, shaking his head. He's being dumb.

 

-

 

Philip felt his heart speed up, biting his lip. Oh god, this was really happening. He could hardly believe it, really. He'd never done something this... taboo, and he'd done some shit.

 

_An Uber would be lovely, actually. Do you want to meet up tomorrow? We can even do it tonight, if night coffees don't bug you too much. I have a paper to write anyway, so a pick me up would be great._

 

Did that come off as too eager? He really wanted to see this guy in person... and get a free coffee, and a free Uber, and possibly the best thing that had happened to him because of college: Being completely broke and then having a cute guy that would make him less broke and fuck him. Fuck him frequently. Goddamn, he was excited.


	3. Chapter 3

**Summary for the Chapter:**

> They actual meet in this one whaaaaaaaaaaattttttttttttttttt

_Tonight actually sounds great. Caffeine stopped affecting me a long time ago. Does 6 work?_

 

Thomas is practically giddy when he sends the message. Shit, what's he going to wear? A suit isn't the kind of thing that you wear to just, like, a random coffee date. He hasn't even  _been_ on an actual date with a stranger since he got right out of college. About the same time he met Hamilton. Speaking of Hamilton, he'd love to see ol' Hammy's reaction to him catching such a nice piece of ass.

 

He decides on a violently purple sweater and jeans that he hasn't worn in a year. While he's pretty sure Philip won't be coming home with him the first time that they ever meet in person, he stocks his top drawer with condoms and a significant amount of lube anyway.

 

Shit. It's actually only 5. He still has a half hour to go before he even should have thought about any of this. Damn, at least he's prepared. 

 

As he's scrolling through his date's profile, he can't help but feel a strange sense of familiarity from some of the pictures. Chocking it up to nothing but nervous energy, Thomas sets his phone on his nightstand in favor of a random novel about the Revolutionary War that he got from office Secret Santa at Christmas. Maybe it was Lee that bought it? Who the fuck knows. 

 

-

 

Philip couldn't help but grin. Dear God. Oh shit, this was actually fucking happening. 

 

_Sounds great. I'll send you where to send the Uber around 5:45_

 

He sends the message and gets up, looking over his outfit in the mirror. His black skinny jeans looked hot, but maybe he should change out of his hoodie. Dress to impress, right? He dug through his closet, twisting his curls around his finger anxiously. He didn't have a ton of clothes, but he had to have at least a nice t-shirt or something. After about fifteen minutes he managed to find a green and very tight t-shirt. It made his waist look smaller, even a little more feminine. He likes it. George wouldn't have. 

 

Smirking a little, he grabbed his jacket but stopped in his tracks when he looked at his phone. Shit. He still had forty-five minutes before he had to meet Thomas. He still did have that paper to write...

 

-

 

By the time 6 rolls around, Thomas is fucking shaking. His driver rolls up to the coffee shop and he steps out after a polite nod. He somehow pulls enough courage to push open the door, a wave of cold air and pretentious indie music hitting him square in the face. He probably couldn't pronounce the band's name even if he knew it or wanted to or even cared. Fucking whippersnappers.

 

It's not what he would usually listen to at all but it's immediately relaxing. This is his escape from Hamilton, this is where he comes to plow through articles in the evenings, and this is where he's going to have coffee with a goddamn supermodel. 

 

He ends up kind of lurking by the entrance, waiting for Philip. He pulls out his phone and does his best to not look like a creep. He honestly has no idea if it's working. The door swings open once more, and there he is. Even prettier in person. The journalist sucks in a sharp breath, locks eyes with the young man, and offers his hand. 

 

"Thomas Jefferson. It's nice to see you in person."

 

-

 

As Philip climbed out of his Uber, he was physically shaking. He couldn't wait for this, but it's more than a little terrifying. He steps into the cafe, a bit surprised when Thomas suddenly introduced himself, stepping back. He laughed a little, hesitantly shaking the offered hand. "I- um, hey." He couldn't help but grin as he looked over the other man, biting his lip. "You look even nicer in person, Mr. Jefferson." 

 

Philip carefully pulled back, glancing to the front of the shop. "Coffee?" He asked quietly, tilting his head in a way that his mother often told him reminded her of a puppy. He didn't mind being a little cute, he could pull Thomas in that way. 

 

"That's what we're here for, isn't it? I'm sorry for scaring you, by the way. I couldn't decide if I should sit or stand. I thought that I might miss you, but now I know that that's not possible. You're incredibly handsome."

 

Pip is entirely aware that the older man is staring. It makes him feel good. They chat a little bit in line, and there's just something about the way that he talks. The way that he drops his 'y's', and the way that he can't let an a and a 'sh' go without an 'r'. He's definitely trying to sound less Southern than what he is.

 

"Mr. Jefferson, where are you from?" The student raises an eyebrow, crossing his arms.

 

"Richmond. I'm just doing my best to not sound like a cousin fucker. It's not workin' is it?"

 


End file.
